in: Advice, Character, Featured

• Last updated: September 25, 2021

Stop Hacking Your Life

Three men standing in science lab and one man taking photo of experiments.

Editor’s Note: This is a guest post from Kyle Eschenroeder.

“There are a thousand hacking at the branches of evil to one who is striking at the root.” –Henry David Thoreau

“100 Life Hacks That Make Life Easier” –Article published on (179k social shares)

As legend has it, Alexander the Great undid the world’s most intricate knot. The Gordian Knot held a royal ox-cart to a post and remained tied for hundreds of years.

Then, in 333 BC, Alexander came along and tried to undo the knot. He, like the hundreds before him, couldn’t loosen it. Did he leave it for others to solve? Of course not! He’s Alexander the Great! He took his sword and solved the problem then and there.

We haven’t stopped swinging swords — and looking for easier, quicker, more direct solutions to life’s knotty problems — since.

A couple thousand years later, in 2004, a fellow named Danny O’Brien mentioned “life hack” in a talk about programmers and the “embarrassing” scripts and shortcuts they use. A hack, especially in computer science, is defined by Wikipedia as an “effective but inelegant solution” to a problem.

In 2005, was created, and the concept took off and no longer centered just on tech shortcuts, but learning easier, niftier ways to do everything from cutting an onion to improving your focus. That same year, the American Dialectic Society named “lifehack” (now one word) as runner-up for its annual “most useful word” award, second only to “podcast.” (Where “love” or “courage” placed on their list I have no idea.)

In 2007 Timothy Ferriss published The 4-Hour Workweek and extended the idea of lifehacking to running a business and creating a leisure-filled lifestyle. Probably 80% of all entrepreneurial and productivity-oriented lifehacks you come across online were popularized by Tim’s book.

In the 2010s, articles, books, and even scientific studies focusing on lifestyle optimization have proliferated. Headlines scream: “You’ve Been Doing This Wrong All Along!” and we dutifully click to figure out how to make the needed improvements. We read up on getting our sleep schedule just right, our diet perfected, and our environment just so, and we tirelessly comply with the advice experts offer by tracking our steps, our breaths, and how much we moved while we snoozed.

All of these lifehacks promise a better life with less effort.

It’s an irresistible offer.

Why untie a knot when you can cut it with your sword?

Two Relationships to Hacks

The hacking tools and tricks.

Many people have had success using these life optimization tools and tricks, and they’re not necessarily a bad thing. Their effect all depends on which of two relationships someone has with hacking:

  1. Hacking for something. When Alexander the Great cut the Gordian Knot he didn’t care about much else besides getting the ox-cart off the pole. Cutting the knot was the best solution to his problem. When a programmer finds a hack that allows him to move forward he has done the same thing. The focus is on an outcome and the hack is a way to get there. This often means solving problems creatively.
  2. Hacking for hacking’s sake. Then there is the person scrolling through Lifehacker collecting listicles. Reading and re-reading the same hacks spewed out a thousand times. This is the person who won’t go to the gym until they know for a fact that they have the “perfect” workout regimen. This is the person who doesn’t start a business because they don’t know how; they always have to do just a little more research before they get going. These are the people who are constantly talking about how they need to get up earlier, to cut out gluten, to implement the Pomodoro technique

Hacking approach can be beneficial; every man should have a little MacGyver in him and keep some duct-tape solutions in his back pocket. And if there’s a better way to cut an onion, by all means, go for it.

But hacking approach invariably leads to a life that’s less optimal, not more. The damage results not so much from the actual hacking practices themselves, but from the mindset their pursuit and adoption begets.

It’s a mindset marked by “Efficiency Paranoia.” You become more focused on hacking — finding just the right tools and environment — than on your goal, and your big-picture progress towards it. You forget that tools must be used to matter. You overlook the fact you are capable of figuring things out on your own (and that the work required to do so can be a great source of pleasure).

The hacking mindset thinks the answer is “out there.” This is why we Google things like “What should I do with my life?” or click on articles that promise “How to Be More Courageous in 5 Easy Steps.”

The hacking mindset tells us that once we master the right seduction techniques we will finally fall in love with the woman of our dreams.

The hacking mindset tells us we will not have to surmount the obstacles on the way to our aims if we can simply find a way around them.

The hacking mindset flatters the part of us who’s lazy, who always wants to take the path of least resistance, who loves feeling superior to the “chumps” who are taking the hard way. But, despite all our new technological advancements, life itself remains stubbornly impervious to hacking. You do not get to cheat death. You do not get to escape being human. You cannot circumvent the universal law which dictates that all goals require work, time, pain, and suffering to attain. The obstacle remains the way.

Once you free yourself from the hacking mindset, you no longer have anxiety that someone out there might have the secret that will finally make everything fall into place. The restless FOMO that comes from thinking there is a more effective way to do something, and the anxiety that you’re not doing life “right,” dissipates. You trust yourself more and become less needy. You begin to effectively assimilate and use information instead of fearfully hoarding it. You enjoy the climb instead of cursing it. And, lo and behold, though you do not take the “optimal” path, you magically, paradoxically, get a whole lot more done.

To liberate ourselves from something that’s so thoroughly ingrained in our culture, we need to learn to see the deleterious ways it manifests itself. So let’s look at six problems presented by the hacking mindset.

Why a Focus on Hacking Leads to a Less Optimal Life

Hacking leads to a less optimal life.

Hacking Stigmatizes Effort

“The whole glory of virtue resides in activity.” –Cicero

If less effort is the goal, exerting effort is a kind of failure.

There is a special breed of “lifestyle designers” who seem to only do things so that they can go travel. (And it seems they only travel for trophy pictures.) Every obligation or responsibility they incur is a failure to lead a free life.

They put together “businesses” that they can automate and never look at again.

They got into this lifestyle because someone scared them of “deferring” the good life until retirement when they won’t be able to appreciate it anyway. Why wait to live!?

The thing is, now they just want to retire immediately. If they had a White Whale then this wouldn’t be an issue.

Instead of having a dream of creating something amazing, their dream is to work from home (and only four hours per week, please).

This doesn’t seem like a compelling aim for a life’s work.

And it certainly doesn’t invigorate us.

God forbid we do anything hard.

God forbid we try more than what is necessary.

Like dogs chasing a car, we aim at an eternal comfort that, if caught, would destroy us.

A focus on hacking makes everything that requires time and toil look undesirable. Yet those are the prerequisites of the pursuit of anything worthwhile. One cannot catch a whale in a net of hacks.

Hacking Undervalues the Obvious and Useful (But Boring) for the New and Ineffectual (But Sexy)

“People say: ‘What good does it do to point out the obvious?’ A great deal of good; for we sometimes know facts without paying attention to them. Advice is not teaching; it merely engages the attention and rouses us, and concentrates the memory, and keeps it from losing grip. We miss much that is set before our very eyes. Advice is, in fact, a sort of exhortation. The mind often tries not to notice even that which lies before our eyes; we must therefore force upon it the knowledge of things that are perfectly well known.” –Seneca, Moral Letters to Lucilius

Everything needs an exclamation mark to be noticed.

Exclamation marks cost advertising dollars though, which means that timeless, but effective advice off which you can’t make a buck gets lost in the noise. You’re never going to see a Super Bowl ad for broccoli, push-ups, or unguided meditation.

The marketing budget for the next easy fix (pharmaceutical stress reduction pill, fat-loss via berry extracts, liposuction, some new diet), on the other hand, is limitless.

It’s the hacks that get the funding. It’s the next ultimate workout program, magic pharmaceutical invention, or method to instant wealth that you’ll pay for.

It’s slightly more nuanced when scientists or academics are doing the selling.

Universities are under extreme pressure to put out exciting new findings. This pressure is passed on to professors who are forced to do “science by PR.” They exaggerate the implications of their findings in order to sell more books or gain more press.

Big Data allows us to draw correlations between anything we want. Data mining isn’t so much mining as it is finding shapes in clouds.

Sometimes a finding makes it through academia intact. Then the journalists get ahold of it…

A possible solution for 2% increase in solar panel effectiveness becomes The Next Clean Energy Revolution is Here!

Everyone loves sexy science.

But, as a rule of thumb, the newest, most hyped information isn’t the most useful.

What is most useful is rarely hidden away behind a pay wall or some esoteric text. More likely it’s in plain sight, it’s been around for a while, and it’s boring.

But it works.

“Take a simple idea and take it seriously.” –Charlie Munger

Hacking Leads To Aimless Optimization

There is no such thing as a naturally occurring aimless life. Aimlessness happens when too many people have convinced you of the importance of too many aims. Aimlessness isn’t just the absence of an aim, it’s the shadow-side of an aim.

“Indefinite attitudes to the future explain what’s most dysfunctional in our world today. Process trumps substance: when people lack concrete plans to carry out, they use formal rules to assemble a portfolio of various options. This describes Americans today. In middle school, we’re encouraged to start hoarding ‘extracurricular activities.’ In high school, ambitious students compete even harder to appear omnicompetent. By the time a student gets to college, he’s spent a decade curating a bewilderingly diverse résumé to prepare for a completely unknowable future. Come what may, he’s ready — for nothing in particular.” —Peter ThielZero to One: Notes on Startups, or How to Build the Future

Perhaps the greatest productivity “hack” is to become what the billionaire investor Peter Thiel would call a “definite optimist.” That means believing in a concrete future and your ability to create it — or at least a part of it.

Many of us are “indefinite optimists” right now. We believe that the world will be better in the future but have no idea what that means. Thiel uses the finance sector to highlight this attitude: You wouldn’t invest if the future seemed bleak, but you don’t need to have a specific vision for what the future actually looks like.

Scrolling through listicles of productivity advice is an act of indefinite optimism. We collect massive amounts of this low-grade information in hopes that one day it will be useful. We go through these lists every day hoping for the thing without considering the source: some blogger who has to write five more articles that day and is desperate for clicks.

A definite optimist wouldn’t do this. Why?

A definite optimist has a White Whale.

Knowing what you want provides a powerful filter against crappy content. Having a definite aim makes it easier to determine what paths aren’t worth going down.

When we optimize for everything we optimize for nothing.

When we try to optimize for life we get into even bigger trouble.

Those who study productivity the most don’t produce the most.

They have nothing to prepare for. There is no context for them to apply anything.

They have made the mistake of believing that you can optimize life. That if they follow the instructions of some study they will find pure bliss. They will finally escape being human.

Without context all we can see is the web of hacks that we’ve created. The perfect routine, the perfect body, and the perfect bank account: all in service of nothing.

Optimization of productivity is like a multiplier. If there is nothing to multiply, you end up at zero. If you have a definite direction you will naturally optimize over time.

Your definite optimism doesn’t even need to be, well, definite. Nobody can predict the future; the point is to have the courage to do so.

Newton cared more about alchemy and Biblical studies than his famous scientific works. After reading these, John Maynard Keynes said, “Newton was not the first of the age of reason, he was the last of the magicians.”

The specific thing that Newton was driven towards wasn’t what mattered for society in the end. It was still crucially important as the thing that drove Newton to do interesting things. Without his interest in the occult we would not have benefited from his other great work.

Aim doesn’t even need to mean that you think you know what will happen. Nassim Taleb suggests we become antifragile in certain areas of our lives. This means benefitting from (often unexpected) volatility. It means being in a position to win from the unknown. This is a specific aim — one that those who would be “ready for anything” ought to consider.

Hacking Distorts Our View of Time

“Thanks to the clock tower, the rhythms of daily life were now dictated by a machine. Over time, people conformed to ever more precisely scheduled routines. Where the priority of the calendar-driven civilization was God, the priorities of the clockwork universe would be speed and efficiency. Where calendars led people to think in terms of history, clocks led people to think in terms of productivity. Time was money. Only after the proliferation of the clock did the word ‘speed’ (spelled spede) enter the English vocabulary.” –Douglas Rushkoff, Present Shock

We feel so much pressure to hack our lives because of the immense responsibility we (and technology we’ve created) have put on the present moment and the need for immediate success. It’s not acceptable to build a business over a decade, it better be profitable in a week.

You can write a novel in November during NaNoWriMo; why take years to create a masterpiece?

The internet makes sure that you have access to anything the moment it crosses your mind. Your digital devices constantly update with what’s happening now. They whip up a faux sense of urgency that must be witnessed or dealt with.

They are violently bringing you back to the present moment. Compare this to a person “being present.” He is not being shocked into the present by alerts. Instead, he is in control of his attention and places it in the present consciously.

To help understand this difference on a deeper level, it’s worth looking at how the Greeks looked at time. There were two types: chronos and kairos.

Chronos is simple. It’s the time measured by the clock tower. Rushkoff says it’s “what we literally mean when we say ‘three o’clock.’ This is time of the clock, meaning belonging to the clock…”

Chronos is what we’re most comfortable with. It is easily measurable so we can pin it down and work with it. We can gauge how we “use” it to make sure everything is just right.

Kairos is more the qualitative side of time. Being qualitative, it demands the human touch. Rushkoff explains:

[Kairos] is usually understood as a window of opportunity created by circumstances, God, or fate. It is the ideal time to strike, to propose marriage, or to take any particular course of action. Carpe diem.

Hacking or optimizing your life is concerned with chronos because that’s the only thing it can be concerned with. There is no clear way to teach kairos without discussing courage, mindfulness, purpose, and humanity. Chronos is more graspable and moldable: make a chart, set the clock for 45 minutes, don’t take meetings, multitask or don’t multitask, on and on.

Kairos is knowing the right time for you while chronos is knowing the time according to the clock. Kairos is knowing when to go in for the kiss while chronos is concerned with your date being on time. Kairos feels that five years is an acceptable amount of time to make a blog profitable; chronos balks at the idea. Kairos understands context, chronos hungers for infinitely more, infinitely faster.

Our chronos-heavy perspective on time doesn’t just cause anxiety; it makes us weak as humans and keeps us stuck in our current circumstances. Rushkoff says this is because:

“It assumes that kairos has no value — that if there is a moment of opportunity to be seized, that moment will break into our flow from the outside, like a pop-up ad on the Web. We lose the ability to imagine opportunities emerging and excitement arising from pursuing whatever we are currently doing, as we compulsively anticipate the next decision point.”

We wait for the email, the text message, the next comment on our new Facebook profile picture. We scroll through Instagram looking for the motivational image we need.

We don’t know what to do with ourselves if our time isn’t being demanded by automated notifications.

Some like to say that we all have the same 24 hours in a day. You and the President. Sure. For someone stuck in chronos this is true. For someone who understands kairos it’s absurd.

Dependence on Replicating the Ideal, Expert-Recommended Circumstances Before Getting Started

air and light and time and space by Charles Bukowski

“– you know, I’ve either had a family, a job,
something has always been in the
but now
I’ve sold my house, I’ve found this
place, a large studio, you should see the space and
the light.
for the first time in my life I’m going to have
a place and the time to

no baby, if you’re going to create
you’re going to create whether you work
16 hours a day in a coal mine
you’re going to create in a small room with 3 children
while you’re on
you’re going to create with part of your mind and your body blown
you’re going to create blind
you’re going to create with a cat crawling up your
back while
the whole city trembles in earthquake, bombardment,
flood and fire.

baby, air and light and time and space
have nothing to do with it
and don’t create anything
except maybe a longer life to find
new excuses

Stephen King wrote Carrie on a makeshift desk set between a washing machine and a dryer. He wrote while his kid cried and his wife banged pots in the nearby kitchen as she prepared dinner.

This should tell you everything you need to know about the requirements of creativity.

Studies come out and tell you that you need to paint your walls a certain color. That you need to sit down at the same place every day (or a different place every day). That you need this or that. Always contradicting, never taking you into consideration.

These studies are concerned with some measurement on some group of people in some study you weren’t involved in.

If you look at the daily rituals of 100 different creative people you’ll find 100 different things that work. For them.

If you know that you must create, then you will. If you feel like you should create, then you’ll find an excuse not to.

When you must create then you have no choice but to find the best environment and ritual for you. These personal environmental hacks are just that: personal.

You must earn the right to hack your creativity. There is no book that can do it for you. No secret method. Just you, honesty, and an aim.

Keep your locus of control on the inside. Scientific studies will try to convince you that you must have everything just so or you won’t be a genius. They will pull your sense of control outside of you until you forget that you have any at all.

If you do the work you’ll find what works for you. Without the work, no amount of studies will teach you what you want to know.

Hacking Favors Irrational Rationality

Focusing on hacking our lives makes it impossible to discern between irrational rationality and rational irrationality.

Irrational rationality is being reasonable at an unreasonable time. It’s relying on logic when your wife is yelling. It’s coming up with “reasonable” excuses for doing something that feels wrong. And it’s trying to figure out ways to be more productive…at a job you hate. It’s trying to hack the thing when what the issue really demands is courage.

Rational irrationality is being unreasonable at the right times. It’s caring “too much” about some trivial detail. It’s putting all your effort into something that might not work. It’s living with purpose when there is no clear reason to do so. It’s putting aside the hacks in favor of something truly difficult.

Rational irrationality is Newton’s obsession with alchemy. It’s Steve Jobs’ demand that the interior of an Apple device be as beautiful as the exterior. It’s writing a novel that probably won’t be published.

It’s what makes life worth living.

These are the moments when you feel you’re doing the right thing even though it’s confusing or angering everyone else. Your aims and methods would never make it onto a list of “How to Optimize X!” But it’s working for you.

The quality of your life depends on moments of taking the leap when the world is telling you not to. These are the moments that we remember for the rest of our lives.

The health of our economy also depends on rational irrationality.

Silicon Valley was built on “irrational” investments.

It takes an organization that can transcend traditional investment rules (hack for short-term profits) in order to truly push technology. Historically, the military has been the only organization to be able to do this consistently.

The Department of Defense needed boundary-pushing electronics to save lives and protect our freedom. A company aimed at maximizing (read “hacking”) profits could never justify this.

Federal sources accounted for over half of the national R&D expenditures in the twenty-five years leading up to 1978. This was only made possible by the rational irrationality that comes with stakes as high as the Soviets threatening US sovereignty.

Imagine stakes this high in your life. When you’re on a mission you wouldn’t dream of hacking your life — of only doing what’s quick and efficient. You use those necessary hacks that will move you towards your goal, sure, but your mindset is focused on the long adventure ahead.

Joseph Campbell’s hero’s journey describes the pain of “knitting together” your dream world and reality. The hero is the one with enough courage to go beyond rationality (what we know can be brought into reality) and come back with something for our world anyway. It’s painful, but it’s more than worthwhile:

For when a heart insists on its destiny, resisting the general blandishment, then the agony is great; so too the danger. Forces, however, will have been set in motion beyond the reckoning of the senses. Sequences of events from the corners of the world will draw gradually together, and miracles of coincidence bring the inevitable to pass. The talismanic ring from the soul’s encounter with its other portion in the place of recollectedness betokens…a conviction of the waking mind that the reality of the deep is not belied by that of common day. This is the sign of the hero’s requirement, now, to knit together his two worlds.

The remainder…is a history of the slow yet wonderful operation of a destiny that has been summoned into life. Not everyone has a destiny: only the hero who has plunged to touch it, and has come up again — with a ring.”

We have rationalized away most good reasons for caring intensely. Newton’s intense drive to solve the mind of God would be looked at as madness now. It seems there are fewer scientific discoveries that will matter widely and last for more than a decade. It doesn’t seem that any book written this year will be read in 100 years.

The modern hero is the one who has the ability to create meaning.

The hero now is the one who can dig down deep and give a damn for no justifiable reason. His ability to maintain virility in the face of an objective purposelessness serves as an inspiration to those around him. He will certainly find hacks along the way, but would never consider hacking the journey itself.

What’s the point? What is there to do?

Two men using hammer for multiple exposures.

“… the labyrinth is thoroughly known; we have only to follow the thread of the hero-path. And where we had thought to find an abomination, we shall find a god; where we had thought to slay another, we shall slay ourselves; where we had thought to travel outward, we shall come to the center of our own existence; where we had thought to be alone, we shall be with all the world.”

–Joseph Campbell, The Hero With A Thousand Faces

What is the one thing that all the weakening effects of our hacking culture outlined above work to undermine?


That’s the heart of the matter.

Focusing on hacking cuts our autonomous legs out from under us. It breeds dependence on expert advice and shortcuts in order to get started and keep moving. It emphasizes new and sexy tips and tricks, while obscuring the simple, obvious advice that could actually save us. It focuses our view on the present, and confuses mere activity with moving towards an ultimate aim. It tells us that obstacles are optional, and that if they are encountered, you can always find a way around them — that only suckers climb mountains when you can take the chairlift.

Counteracting the self-reliance-sapping effects of hacking culture isn’t easy; the very nature of the problem denies any prescription, much less a hackable solution. Still, in relation to the six problems we discussed above, several general principles/stances can be recommended:

  • Maintaining a strong, centered posture even as quick fixes and silver bullets are continually thrown at you, using them only when useful, and embracing the effort that’s needed when they’re not.
  • Focusing on obvious, time-tested advice, and what you have found works for you, rather than being distracted by what’s new and sexy.
  • Having a clear aim and avoiding the temptation to optimize for zero.
  • Remembering kairos and that time is not just what your clock can measure.
  • Valuing your own personal experience over what a study says, and feeling free to do your own experiments.
  • Having the courage to care about what you care about, and to do things your way, whether it makes sense to others or not.

The crux of one’s hacking counter-stance must ultimately rest on the prioritization of right action over abstraction. I say “right action” instead of “action” as a reminder that busyness is worse than doing nothing. It feels productive while your soul shrinks and the important things go left undone.

Perhaps your first action must be to create a whole new approach to life — a new mindset that undoes that which has been ingrained since youth.

When we were in school they gave us problems to solve.

When we got jobs they gave us tasks to complete.

But when we graduated, got fired, fell in love, started businesses, had kids?

There was no absolute right answer.

And so we had to write our own questions.

That’s the hardest thing to do when you’ve spent your whole life finding answers to other peoples’ equations.

The hacking mind is obsessed with answering questions. It makes your life small by forgetting there are other questions out there to ask.

The hacking mind will have you think that your life can be measured and thus optimized. That your existence is something to be charted and cheated.

When you start writing your own questions you can reject this notion.

Instead of googling what to do with your life you can live.

Instead of trying to sleep according to the opinions of some scientists you can go to bed when you want.

Instead of reading a book written by a bad business consultant you can read a novel.

Instead of pretending like you want something you can actually want something.

Instead of learning how to manipulate women you could sack up and talk to one.

In short, you can be you.

You know what you want in life.
You like eating the good stuff.
You like challenging things.
You like taking the long way home from work.
You don’t actually want that car.
You can’t be hacked.

Because hacks are small.

And you are big.


Kyle Eschenroeder is a writer and entrepreneur. He’s partnered with Art of Manliness to publish The Pocket Guide to Action: 116 Meditations on the Art of Doing. Once a week he sends out a letter with 5 important ideas, click here if you’d like to be included. 

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